CAS 89-57-6|mesalazine|5-Amino-2-hydroxybenzoic acid|5-amino-2-hydroxybenzoic acid|5-aminosalicylic acid|5-Amino-2-hydroxybenzoic acid 97%|5-氨基水杨酸|5-AS|5-氨基-2-羟基苯甲酸|5-Aminosalicylic acid|...

基本信息

化学结构

分子式

C₇H₇NO₃

分子量

153.13538

精确质量

153.04259309

电荷

InChI

InChI=1S/C7H7NO3/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,9H,8H2,(H,10,11)

InChIKey

KBOPZPXVLCULAV-UHFFFAOYSA-N

Canonic Smiles

Nc1ccc(c(c1)C(=O)O)O

Isomeric Smiles

Oc1c(cc(N)cc1)C(=O)O

计算属性

JChem

LogD (pH = 7.4)

-1.72

LogD (pH = 5.5)

-0.43

Log P

-0.29

可自由旋转的化学键

质子供体

质子受体

里宾斯基五规则

true

Acid pKa

2.02

极化表面积

83.55

极化性

14.26

摩尔折射率

40.00

LOG S

-0.92

数据来源

名称和标识

IUPAC传统名

mesalazine 5-amino-2-hydroxybenzoic acid

别名

5-Amino-2-hydroxybenzoic acid5-aminosalicylic acid5-Amino-2-hydroxybenzoic acid 97%5-氨基水杨酸5-AS5-氨基-2-羟基苯甲酸5-Aminosalicylic acid氨水杨酸5-AMINOSALICYLIC ACIDMesalamine5-Amino-2-hydroxybenzoic acidAsacolP 5-aminosalicylic acidMesalazineMesalamineRowasaMesasalMesalazineMesalazineFisalamineAsacolitinClaversalAsalitSalofalk5-ASAPentasa5-aminosalicylate5-氨基水杨酸Mesalamine氨水杨酸Mesalazinemesalaminem-Aminosalicylic acid5-ASA5-Aminosalicylic acid3-carboxy-4-hydroxyanilinep-Aminosalicylsaeure

IUPAC标准名

5-amino-2-hydroxybenzoic acid

商标名

CanasaMesasalPentasaAsacolAsacolitinLixacolClaversalSalofalkRowasaFisalamineIialda

API名称

Mesalazine

国际非专利药品(INN)

mesalazinemesalazinamesalazinum

名称和标识

数据登录号

化合物性质

药理学性质

生物活性机理

Cyclooxygenase inhibitor

Prostaglandin antagonist

化合物性质

分子相关蛋白质

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分子图谱

暂无数据

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描述信息

DrugBank

DB00244

Drug Groups

approved

Description

An anti-inflammatory agent, structurally related to the salicylates, which is active in inflammatory bowel disease. It is considered to be the active moiety of sulphasalazine. (From Martindale, The Extra Pharmacopoeia, 30th ed)

Indication

For the treatment of active ulcerative proctitis.

Pharmacology

Mesalazine (INN, BAN), also known as Mesalamine (USAN) or 5-aminosalicylic acid (5-ASA), is an anti-inflammatory drug used to treat inflammation of the digestive tract (Crohn's disease) and mild to moderate ulcerative colitis. Mesalazine is a bowel-specific aminosalicylate drug that is metabolized in the gut and has its predominant actions there, thereby having fewer systemic side effects. As a derivative of salicylic acid, 5-ASA is also an antioxidant that traps free radicals, which are potentially damaging by-products of metabolism.

Toxicity

Oral, mouse: LD₅₀ = 3370 mg/kg; Oral, rat: LD₅₀ = 2800 mg/kg; Skin, rabbit: LD₅₀ = >5 gm/kg. There have been no documented reports of serious toxicity in man resulting from massive overdosing with mesalamine. Under ordinary circumstances, mesalazine absorption from the colon is limited.

Affected Organisms

Humans and other mammals

Biotransformation

Rapidly and extensively metabolized, mainly to N-acetyl-5-ASA (Ac-5-ASA) in the intestinal mucosal wall and the liver. Ac-5-ASA is further acetylated (deactivated) in at least 2 sites, the colonic epithelium and the liver.

Absorption

20 to 30% absorbed following oral administration. 10 to 35% absorbed from the colon (rectal suppository) - extent of absorption is determined by the length of time the drug is retained in the colon.

Half Life

The mean elimination half-life was 5 hours for 5-ASA and six hours for N-acetyl-5-ASA following the initial dose. At steady state, the mean elimination half-life was seven hours for both 5-ASA and N-acetyl-5-ASA.

Protein Binding

About 80% of N-Ac-5-ASA is bound to plasma proteins, whereas 40% of mesalamine is protein bound.

Elimination

Approximately 28% of the mesalamine in Asacol tablets is absorbed after oral ingestion, leaving the remainder available for topical action and excretion in the feces.
It is excreted mainly by the kidney as N-acetyl-5-aminosalicylic acid.

References

• [Link]

External Links

• [Wikipedia]

• [RxList]

• [PDRhealth]

Selleck Chemicals

S1681

Research Area: Inflammation
Biological Activity:
Mesalamine (Lialda, Apriso) is an anti-inflammatory compound used to treat inflammation of the digestive tract ulcerative colitis and mild-to-moderate Crohn’s disease. Mesalamine (Lialda, Apriso) is a bowel-specific aminosalicylate drug that acts locally in the gut and has its predominant actions there, thereby having few systemic side effects. As a derivative of salicylic acid, 5-ASA is also thought to be an antioxidant that traps free radicals, which are potentially damaging byproducts of metabolism. [1]

MP Biomedicals

02154770

(5-Amino-2-hydroxybenzoic acid) Purity: 99% Off-white to gray powder.

05215090

MP Biomedicals Rare Chemical collection

Sigma Aldrich

A3021

Application
5-氨基水杨酸是一种适用于 ELISA 分析的过氧化物酶底物。该底物生成棕色的可溶性终产物，该产物可通过分光光度法在 450nm 处读取。加入 3N NaOH 可终止反应，然后在 550nm 处进行读取。

A3537

A6178

Application
5-氨基水杨酸是一种适用于 ELISA 分析的过氧化物酶底物。该底物生成棕色的可溶性终产物，该产物可通过分光光度法在 450nm 处读取。加入 3N NaOH 可终止反应，然后在 550nm 处进行读取。
Quantity
Contains 100 mg substrate per tablet.

A79809

Application
5-氨基水杨酸是一种适用于 ELISA 分析的过氧化物酶底物。该底物生成棕色的可溶性终产物，该产物可通过分光光度法在 450nm 处读取。加入 3N NaOH 可终止反应，然后在 550nm 处进行读取。
包装
100 g in poly bottle
5 g in glass bottle

09407

Application
5-氨基水杨酸是一种适用于 ELISA 分析的过氧化物酶底物。该底物生成棕色的可溶性终产物，该产物可通过分光光度法在 450nm 处读取。加入 3N NaOH 可终止反应，然后在 550nm 处进行读取。
Other Notes
Peroxidase substrate suitable for use in ELISA procedures1

73530

09410

09409

TRC

M258100

The active metabolite of Sulfasalazine (S699084). Anti-inflammatory (gastrointestinal).

ChEBI

CHEBI:6775

A monohydroxybenzoic acid that is salicylic acid substituted by an amino group at the 5-position.

描述信息

参考文献

PubChem文献

数据源提供

• Link

• http://en.wikipedia.org/wiki/Mesalazine

• Friedman, G., et al.: Am. J. Gastroenterol., 81, 141 (1986)

• Tursi A., Expert Opin. Pharmacother., 6, 69 (2005)

• Georgieva, M., Anal. Chim. Acta, 1978, 101, 139

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 1121C, (nmr)

• CRC Atlas of Spectral Data and Physical Constants, b848, (ir, uv)

• Weil, H. et al., Ber., 1922, 55, 2664, (synth)

• Myers, B. et al., Gut, 1987, 28, 196, (metab)

• Dobson, A.J. et al., Acta Cryst. C, 1998, 54, 1632-1634, (cryst struct)

• Lepri, L. et al., J. Chromatogr., 1974, 88, 331

• Dash, A.K. et al., Anal. Profiles Drug Subst., 1998, 25, 209-242, (rev, pharmacol)

• Drain, D.J. et al., J.C.S., 1949, 1498-1503, (N-Ac)

• Hoult, J.R.S., Drugs, 1986, 32, 18, (rev)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 8427

• Prakash, A. et al., Drugs, 1999, 57, 383-408, (rev)

• Clemett, D. et al., Drugs, 2000, 59, 929-956

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 219B, (ir)

• Shavel, J. et al., J. Am. Pharm. Assoc., 1953, 42, 402; CA, 48, 9325

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, AMM500

参考文献

生物活性

PubChem BioAssay

生物活性

名称和标识

IUPAC传统名

mesalazine 5-amino-2-hydroxybenzoic acid

别名

IUPAC标准名

5-amino-2-hydroxybenzoic acid

商标名

CanasaMesasalPentasaAsacolAsacolitinLixacolClaversalSalofalkRowasaFisalamineIialda

API名称

Mesalazine

国际非专利药品(INN)

mesalazinemesalazinamesalazinum

描述信息

DrugBank

DB00244

Drug Groups

approved

Description

Indication

For the treatment of active ulcerative proctitis.

Pharmacology

Toxicity

Affected Organisms

Humans and other mammals

Biotransformation

Absorption

20 to 30% absorbed following oral administration. 10 to 35% absorbed from the colon (rectal suppository) - extent of absorption is determined by the length of time the drug is retained in the colon.

Half Life

Protein Binding

About 80% of N-Ac-5-ASA is bound to plasma proteins, whereas 40% of mesalamine is protein bound.

Elimination

References

• [Link]

External Links

• [Wikipedia]

• [RxList]

• [PDRhealth]

Selleck Chemicals

S1681